Tigecycline

Modify Date: 2025-08-20 09:19:51

Tigecycline Structure
Tigecycline structure
 Common Name Tigecycline
CAS Number 220620-09-7 Molecular Weight 585.649
Density 1.5±0.1 g/cm3 Boiling Point 890.9±65.0 °C at 760 mmHg
Molecular Formula C29H39N5O8 Melting Point 164-166°C
MSDS N/A Flash Point 492.6±34.3 °C
Symbol GHS07 GHS08
GHS07, GHS08		 Signal Word Danger

 Use of Tigecycline


Tigecycline is a first-in-class, broad spectrum antibiotic with activity against antibiotic-resistant organisms.Target: AntibacterialTigecycline is active against a broad range of gram-negative and gram-positive bacterial species including clinically important multidrug-resistant nosocomial and community-acquired bacterial pathogens. Tigecycline has been shown to inhibit the translation elongation step by binding to the ribosome 30S subunit and preventing aminoacylated tRNAs to accommodate in the ribosomal A site [1]. Tigecycline has also been found to be effective for the treatment of community- as well as hospital-acquired and ventilator-associated pneumonia and bacteremia, sepsis with shock and urinary tract infections. Tigecycline appears to be a valuable treatment option for the management of superbugs, especially where conventional therapy has failed [2].Fifteen patients received tigecycline for 16 episodes of CPKP infection. The main infections were pneumonia (31%), urinary tract infection (31%), peritonitis (20%), catheter-related bacteraemia (12%), and meningitis (6%). Most infections were complicated with severe sepsis (44%), septic shock (12%), and/or bacteraemia (19%). The daily maintenance dose of tigecycline was 200 mg in 10 episodes and 100 mg in 6 episodes. The overall 30-day mortality rate was 25%. Univariate analysis showed that mortality was significantly associated (p < 0.01) with mean APACHE II and SOFA scores and the presence of immunosuppression, but not with the tigecycline dose [3].

 Names

Name tigecycline
Synonym More Synonyms

 Tigecycline Biological Activity

Description Tigecycline is a first-in-class, broad spectrum antibiotic with activity against antibiotic-resistant organisms.Target: AntibacterialTigecycline is active against a broad range of gram-negative and gram-positive bacterial species including clinically important multidrug-resistant nosocomial and community-acquired bacterial pathogens. Tigecycline has been shown to inhibit the translation elongation step by binding to the ribosome 30S subunit and preventing aminoacylated tRNAs to accommodate in the ribosomal A site [1]. Tigecycline has also been found to be effective for the treatment of community- as well as hospital-acquired and ventilator-associated pneumonia and bacteremia, sepsis with shock and urinary tract infections. Tigecycline appears to be a valuable treatment option for the management of superbugs, especially where conventional therapy has failed [2].Fifteen patients received tigecycline for 16 episodes of CPKP infection. The main infections were pneumonia (31%), urinary tract infection (31%), peritonitis (20%), catheter-related bacteraemia (12%), and meningitis (6%). Most infections were complicated with severe sepsis (44%), septic shock (12%), and/or bacteraemia (19%). The daily maintenance dose of tigecycline was 200 mg in 10 episodes and 100 mg in 6 episodes. The overall 30-day mortality rate was 25%. Univariate analysis showed that mortality was significantly associated (p < 0.01) with mean APACHE II and SOFA scores and the presence of immunosuppression, but not with the tigecycline dose [3].
Related Catalog
References

[1]. Seputiene V, et al. Tigecycline - how powerful is it in the fight against antibiotic-resistant bacteria? Medicina (Kaunas). 2010;46(4):240-8.

[2]. Bhattacharya M, et al. Tigecycline. J Postgrad Med. 2009 Jan-Mar;55(1):65-8.

[3]. Moreno BB, et al. Tigecycline therapy for infections due to carbapenemase-producing Klebsiella pneumoniae in critically ill patients. Scand J Infect Dis. 2013 Dec 20.

 Chemical & Physical Properties

Density 1.5±0.1 g/cm3
Boiling Point 890.9±65.0 °C at 760 mmHg
Melting Point 164-166°C
Molecular Formula C29H39N5O8
Molecular Weight 585.649
Flash Point 492.6±34.3 °C
Exact Mass 585.279846
PSA 205.76000
LogP -1.30
Vapour Pressure 0.0±0.3 mmHg at 25°C
Index of Refraction 1.675
Storage condition Amber Vial, -20°C Freezer

 Safety Information

Symbol GHS07 GHS08
GHS07, GHS08
Signal Word Danger
Hazard Statements H319-H360
Precautionary Statements P201-P280-P305 + P351 + P338-P308 + P313
Hazard Codes Xn
Safety Phrases S24/25
RIDADR UN 3077 9 / PGIII
WGK Germany 3
HS Code 3004909090

 Synthetic Route

9-chloroacetamidominocycline structure

9-chloroacetami...

CAS#:156263-28-4

tert-Butylamine structure

tert-Butylamine

CAS#:75-64-9

~89%

Tigecycline Structure

Tigecycline

CAS#:220620-09-7

Literature: SANDOZ AG Patent: WO2009/92680 A2, 2009 ; Location in patent: Page/Page column 7 ;
t-butylacetyl chloride structure

t-butylacetyl c...

CAS#:7065-46-5

9-Animominocycline structure

9-Animominocycline

CAS#:149934-19-0

~%

Tigecycline Structure

Tigecycline

CAS#:220620-09-7

Literature: Bioorganic and Medicinal Chemistry Letters, , vol. 9, # 10 p. 1459 - 1462

 Customs

HS Code 3004909090

 Synonyms

WAY-GAR 936
TIGECYCLINE POWDER
9-t-Butylglycylamido-minocycline hydrate
2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-9-((((1,1-dimethylethyl)amino)acetyl)amino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4S,4aS,5aR,12aS)-
Tigercycline
(4S,4aS,5aR,12aS)-9-{[(tert-butylamino)acetyl]amino}-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
2-naphthacenecarboxamide, 4,7-bis(dimethylamino)-9-[[[(1,1-dimethylethyl)amino]acetyl]amino]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4S,4aS,5aR,12aS)-
2-NAPHTHACENECARBOXAMIDE
(4S,4aS,5aR,12aS)-9-[(N-tert-Butylglycyl)amino]-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
Glycylcycline
(4S,4aS,5aR,12aS)-4,7-Bis(dimethylamino)-3,10,12,12a-tetrahydroxy-9-{[N-(2-methyl-2-propanyl)glycyl]amino}-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-tetracenecarboxamide
2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-9-[[2-[(1,1-dimethylethyl)amino]acetyl]amino]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4S,4aS,5aR,12aS)-
Tygacil
MFCD00935753
Tigecycline
TIGECYCLINE GLYCYLCYCLINE
Tegecycline
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